(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(thiophen-3-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

ID: ALA4559996

PubChem CID: 3010825

Max Phase: Preclinical

Molecular Formula: C14H14N4O4S

Molecular Weight: 334.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(-c4ccsc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H14N4O4S/c19-3-8-11(20)12(21)14(22-8)18-6-17-10-9(7-1-2-23-4-7)15-5-16-13(10)18/h1-2,4-6,8,11-12,14,19-21H,3H2/t8-,11-,12-,14-/m1/s1

Standard InChI Key:  UXKNTUXJYSDVTH-LHNIVKCTSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    4.9948  -13.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4890  -12.1323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433  -12.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567  -12.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076  -14.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2271  -16.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2953  -14.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820  -12.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614  -13.1796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4704  -14.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9797  -15.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7767  -15.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1982  -15.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721  -11.8453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262  -15.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4755  -12.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7772  -11.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7504  -13.3606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7858  -10.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4572  -10.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2150   -9.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937   -9.6123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1286  -10.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  1
 10  7  1  6
  5 13  1  0
 16  2  1  0
 13 15  1  1
 11  6  1  6
 18 16  2  0
  8  9  1  0
  4 14  1  0
 14  8  2  0
  2 17  2  0
  4 17  1  0
  9  3  1  0
 11 10  1  0
  4  3  2  0
 15 12  1  0
  3 18  1  0
 13 11  1  0
 10  1  1  0
  1  5  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 19  2  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559996

   9-beta-D-ribofuranosyl-6-(thiophen-3-yl)-9H-purine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 334.36

Molecular Weight (Monoisotopic): 334.0736

AlogP: 0.17

#Rotatable Bonds: 3

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 1.72

CX LogP: -0.04

CX LogD: -0.04

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 0.18

References

1. Crespo RA, Dang Q, Zhou NE, Guthrie LM, Snavely TC, Dong W, Loesch KA, Suzuki T, You L, Wang W, O'Malley T, Parish T, Olsen DB, Sacchettini JC..  (2019)  Structure-Guided Drug Design of 6-Substituted Adenosine Analogues as Potent Inhibitors of Mycobacterium tuberculosis Adenosine Kinase.,  62  (9): [PMID:31002508] [10.1021/acs.jmedchem.9b00020]

Source

Source(1):

• Scientific Literature